Are You Up For It? The First Date

Hey guys, this one's for you!

You’ve been chatting or emailing a woman on your matching site and feel there’s an undeniable spark. So how does one go about setting up that first date?

There are some things to think about: Location, who will pay, how long will you meet.

Throw out a couple of ideas and see if she “bites”: “I have tomorrow night and Friday night free; how about meeting for a drink downtown after work?” or “Care to grab a cup of joe one morning this weekend?” Give options so that if she isn’t available on the day you suggest, she realizes that you are flexible and is free to suggest another time. Perhaps she doesn’t feel comfortable with drinks, but “coffee” is more up her alley. Suggest options!

It’s always a good idea to have a phone number when planning to meet in person, just in case one of you has to back out at the last minute. If one of you doesn’t feel comfortable with this, most online dating sites have chat/email features that can be linked to your smart phone with pop up notifications, so it’s really not unlike texting. If your date is tech-savvy, this can work just as well as texting, as long as you are clear that this is where you will contact them if something goes awry before meeting time.

Some people like to talk on the phone first; others want to see the person with the voice all at once, so figure this out in advance. Usually you will only use the phone number to text and say you are late or (hopefully) on time, and later, if the date doesn’t go well, you’ll respectfully erase it from your contacts and not become a stalker. Add first dates under your contacts as, for example, “Betty OKCupid” or “Cynthia Match” or “POF Sue”. You really don’t want to share your last name up front; retain some anonymity until you at least meet in person.

Set a time limit on your first date, even if you really have all afternoon free. This way if you don’t feel that chemistry, you have an excuse to leave. You can say that you have an hour lunch break, but if things are going well, it will be flattering to her that you can change your plans to spend more time with her.

As far as location, public places are always best. If you drive your own vehicle, than you can leave whenever you want—not that you will be a jerk and walk out in the middle of a date, but it happens in extreme situations. Don’t under any circumstances pick up your date, no matter what the situation. Strictly speaking, this is a stranger, really, and you want to play it safe.

Try a trendy coffee shop where you can blend in and not feel on stage with other people watching you. A casual lunch is always non-threatening and isn’t as “invested” as a dinner date. If you do meet for food in the evening because the time works better, make it light and informal, perhaps someplace trendy but casual.

For the first date, I personally always plan to pay for myself; that way I don’t feel I owe my date anything (if you know what I mean). I always insist, and only back down if my date likewise insists. This can be a tricky area for guys. While not all guys can afford to pay for all dates, it speaks volumes up front if you are pretty sure this is a lady you’d like to impress. Unfortunately, you may risk being dubbed as cheap by more traditional women.

To keep a date cheap, you can arrive early and already be at your table with your coffee and a book, implying that she, too, will buy her own and meet you at the table. Again, a truly chivalrous man would walk up to the counter with her and buy her a drink, but there are options.

Likewise, it says something about a lady if she graciously accepts your offer but then adds, “I’ll buy next time.” It implies that she appreciates you AND wants to see you again.

If you decide to meet for a drink in the evening, go against all impulses to get drunk. If you are serious about dating, you probably are not going to take her home with you afterwards, and you want to appear gentlemanly. This is not the time to lose your wits in one too many glasses of alcohol. There’s usually a good reason not to be TOO loose with your tongue. You want to keep swearing to a minimum, as you’re out to make a good first impression. And you don’t want to appear to be an alcoholic, of course, because you loose your control of a situation. If you truly want a second date, keep it to one or two drinks. A water back-up is always an option.

A first date should include plenty of back-and-forth conversation. Some people who get nervous tend to talk too much about themselves, then walk away with the realization that they forgot to ask anything about their date. Yes, it’s easier to talk about yourself—after all, you are an expert on the subject!

However, come prepared with a mental list of things you would like to know more about and don’t let your own gabbing deter you from finding out about HER. Do your research and reread her profile again before your date, and refer to it from time to time. For example, “You said you like to run marathons. What’s the last one you did and how did you do?” or “So you love animals. Do you have any pets?” Be sure you aren’t asking questions that are already answered in her profile or you’ll appear unprepared. Perhaps “What kind of a dog do you have and how old is it?” is more appropriate. People love to talk about their animals like they like to talk about their kids.

Try to go with the flow of the conversation but still keep in mind what you’d like to know. You don’t want to make it seem like an interview, so keep your questions light. Perhaps you find yourself talking about a family reunion you just attended. You can then segue into, “So, do you have a small family or a large one?” and “Are you close to them?” and then throw in some unexpected queries: “So who is your favorite sibling and why?” Be an interesting conversationalist by being prepared.

On your first date, PUT THE PHONE AWAY! Even a beep indicating you have a text or voice message can be very distracting. And god forbid you answer your phone, you risk putting out the vibe that anyone on the other end of that phone is more important than the woman sitting in front of you. If you need to have your phone on for a special reason (perhaps you’re waiting to hear if your bid on a house was accepted) tell her in advance. If your kids are home alone and may call, mention that you may have to take a call from home. But unless there are extreme cases, always put all of your focus on the date in front of you.

Speaking of which, use eye contact! If you are not comfortable doing this, practice it with friends or in business conversations. It’s so important. They say the eyes are your window to the soul. Let her know that you find her every word fascinating by watching the way she expresses herself as she speaks.

Ending a first date can be the indicator of things to come (or not to come). A hug is generally a nice wrap up, whether you had a great time or just enjoyed the conversation. If you would like to see her again, definitely say so, but be prepared for a general “OK, sure” even if she is not interested. She may not want to let you down. A kiss on the cheek while hugging is your next best bet, if you aren’t quite confident of going for the full kiss—which should be avoided unless there is undeniable chemistry, and you have to admit, that’s not always a sure thing.

If you are really into her, you will tell her again afterwards. A text that says, “That was fun! Let’s do it again soon” will be easier for her to respond to if you suggest a date and time like “next week—how about Wednesday evening?” Of course if she couldn’t let you down in person, she may be more comfortable doing so by text, so be prepared. I’ve learned that I can sit and talk to someone for HOURS and would love to be friends with them, but being that I already have friends like that, I have to pass if there is no real chemistry.

The important thing to remember when you’ve been turned down is to take the rejection gracefully. Don’t insult, say she’s missing out on a good thing, or try to convince her otherwise. If she is swayable, a basic, “It was a great experience getting to know you. Good luck and let me know if anything changes” is most likely to make her think you’ve got the stuff if she does reconsider.

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Your coach,

Delaney